4812-40-2

Basic information

• Product Name: 1-(2-HYDROXYETHYL)-2-HYDROXYMETHYL-5-NITROIMIDAZOLE
• Synonyms: 2-hydroxymethyl-5-nitro-imidazole-1-ethano;MNZOH;1-(2-HYDROXYETHYL)-2-HYDROXYMETHYL-5-NITROIMIDAZOLE;HYDROXY METRONIDAZOLE;METRONIDAZOLE-OH;1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole, Hydroxymetronidazole, MNZOH;4-Hydroxy-2-methyl-5-nitro-1H-imidazole-1-ethanol;Metronidazole-OH,1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole, Hydroxymetronidazole, MNZOH
• CAS NO: 4812-40-2
• Molecular Formula: C6H9N3O4
• Molecular Weight: 187.15
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 4812-40-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 118-121°C
• Boiling Point: 321.89°C (rough estimate)
• Flash Point: 241.2°C
• Appearance: /
• Density: 1.4796 (rough estimate)
• Vapor Pressure: 7.73E-10mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 13.28±0.10(Predicted)
• CAS DataBase Reference: 1-(2-HYDROXYETHYL)-2-HYDROXYMETHYL-5-NITROIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-HYDROXYETHYL)-2-HYDROXYMETHYL-5-NITROIMIDAZOLE(4812-40-2)
• EPA Substance Registry System: 1-(2-HYDROXYETHYL)-2-HYDROXYMETHYL-5-NITROIMIDAZOLE(4812-40-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: NI5568000
• Hazardous Substances Data: 4812-40-2(Hazardous Substances Data)

Usage

Description

Hydroxy metronidazole is a metabolite of metronidazole. Metronidazole belongs to the nitroimidazole class of drugs. In agricultural production, it is often used as a drug to expel parasites in animals. After being added to animal feed, metronidazole remains in eggs. Because metronidazole has a variety of toxic and side effects on the human body, especially its potential carcinogenicity and hereditary mutation effects, and metronidazole can be rapidly distributed throughout the body after entering the human body, so the residual metronidazole and its metabolites in eggs inspection is necessary.

Chemical Properties

Off-White Solid

Uses

Hydroxymetronidazole (Metronidazole-OH) is a metabolite of Metronidazole belonging to the class of nitroimidazoles. Hydroxymetronidazole can be used for the research of certain bacterial and protozoal diseases in poultry, swine dysentery and genital trichomoniasis in cattle.

Definition

ChEBI: Metronidazole-OH is a member of imidazoles and a C-nitro compound.

Biological Activity

Hydroxymetronidazole is an active metabolite of the antibiotic metronidazole (Item No. 9002409). It is formed from metronidazole primarily by the cytochrome P450 (CYP) isoform CYP2A6. Hydroxymetronidazole is active against B. fragilis, B. thetaiotaomicron, B. distasonis, and B. ovatus (MICs = 1, 2, 1, and 2 μg/ml, respectively). It has been found in pork and porcine plasma.

InChI:InChI=1/C6H9N3O4/c10-2-1-8-5(4-11)7-3-6(8)9(12)13/h3,10-11H,1-2,4H2

Upstream product

• 147124-51-4 methyl-(2-hydroxymethyl-5-nitro)imidazolylacetate 
• 1016-40-6 ethyl 2-(2-methyl-5-nitro-1H-imidazole-1-yl)acetate 
• 147124-49-0 ethyl-(2-bromomethyl-5-nitro)imidazolylacetate 
• 147124-50-3 (2-Hydroxymethyl-5-nitro-imidazol-1-yl)-acetic acid 
• 443-48-1 metronidazole 

Relevant articles and documents

A comparative study of precision cut liver slices, hepatocytes, and liver microsomes from the Wistar rat using metronidazole as a model substance

1. Metronidazole is metabolized by rat liver in vitro models to form a hydroxy metabolite, an acetic acid metabolite, a glucuronic acid conjugate, and a sulphate conjugate; 2. Four different in vitro systems for investigation of drug metabolism based on liver preparations from the male Wistar rat have been investigated. 3. An incubation system where liver slices are Incubated in 12-well culture plates was evaluated with respect to metabolism of metronidazole. Optimal viability was observed for a time period of up to 24 h. The Michaelis-Menten parameters for the metabolism of metronidazole in liver slices were calculated and the intrinsic clearance values compared with the values determined in hepatocytes incubated in suspension,It was found that the intrinsic clearance with respect to formation of oxidative metabolites, the hydroxy metabolite, and the acetic acid metabolite correlated, whereas the intrinsic clearance with respect to formation of the glucuronic acid conjugate was lower in slices compared with hepatocytes. 4. The metabolism of metronidazole in liver slices, in hepatocytes in primary monolayer culture, in hepatocytes incubated in suspension, and in liver microsomes was compared. All the incubations were performed under identical incubation conditions including the same incubation medium. The trend observed was that the initial metabolic rates of the production of the hydroxy metabolite, the glucuronic acid metabolite, and the acetic acid metabolite of metronidazole were higher in microsomes than in the other liver preparations. The metabolic rates in hepatocytes in primary culture and in suspension with respect to the oxidative metabolites were higher than in liver slices. The metabolic turnover observed in liver slices was predicted to correlate with in vivo data earlier obtained for rat.